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DFT Studies on Hydrolyses of Dimethylchlorothiophosphate

  • Park, Young-Hee (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University) ;
  • Lee, Oh-Seuk (Department of Chemistry, Andong National University) ;
  • Koo, In-Sun (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University) ;
  • Yang, Ki-Yull (Department of Chemistry Education and Research Institute of Natural Science, Gyeongsang National University) ;
  • Lee, Ik-Choon (Department of Chemistry, Inha University)
  • Published : 2006.11.20

Abstract

Keywords

References

  1. Baranskii, V. A.; Eliseeva, G. D.; Sukhorukova, N. A. J. Gen. Chem. USSR 1988, 58, 687
  2. Dixon, B. G.; Au, A. T. Tetrahedron 1986, 42, 1123 https://doi.org/10.1016/S0040-4020(01)87516-5
  3. Kazanov, G. M.; Sergeeva, V. S.; Efremenko, E. N.; Alexandrova, L.; Varfolomeev, S. D.; Ryabov, A. D. Angew. Chem. Int. Ed. 2000, 39, 3115
  4. Gysin, H.; Margot, A. J. Agr. Food Chem. 1958, 6, 900 https://doi.org/10.1021/jf60094a001
  5. Gomaa, H. M.; Suffet, I. H.; Faust, S. D. Residue Reviews 1969, 29, 171
  6. Muhlmann, R.; Schrader, G. Z. Naturforsch 1957, 12b, 196
  7. Zhang, Y.-L.; Hollfelder, F.; Gordon, S. J.; Chen, L.; Keng, Y.-F.; Wu, L.; Herschlag, D.; Zhang, Z.-Y. Biochemistry 1999, 38, 12111 https://doi.org/10.1021/bi990836i
  8. Frey, P. A.; Sammons, R. D. Science 1985, 228, 541 https://doi.org/10.1126/science.2984773
  9. Schmidt, M. W.; Gordon, M. S. J. Am. Chem. Soc. 1985, 107, 1922 https://doi.org/10.1021/ja00293a021
  10. Lee, I.; Kim, C. K.; Li, H. G.; Sohn, C. K.; Kim, C. K.; Lee, H. W.; Lee, B.-S. J. Am. Chem. Soc. 2000, 122, 11162 https://doi.org/10.1021/ja001814i
  11. Lee, O. S.; Yang, K.; Kang, K. D.; Koo, I. S.; Kim, C. K.; Lee, I. J. Comput. Chem. 2004, 25, 1740 https://doi.org/10.1002/jcc.20104
  12. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, F. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adame, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, Revision A.7.; Gaussian, Inc.: Pittsburgh, PA, 1998
  13. Becke, A. D. J. Chem. Phys. 1933, 98, 5648 https://doi.org/10.1063/1.464913
  14. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785 https://doi.org/10.1103/PhysRevB.37.785
  15. Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comp. Chem. 1996, 17, 49 https://doi.org/10.1002/(SICI)1096-987X(19960115)17:1<49::AID-JCC5>3.0.CO;2-0
  16. Schlegel, H. B. Theor. Chim. Acta 1984, 66, 33
  17. Onsager, L. J. Am. Chem. Soc. 1936, 58, 1486 https://doi.org/10.1021/ja01299a050
  18. Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1991, 113, 4776 https://doi.org/10.1021/ja00013a010
  19. Wong, M. W.; Frisch, M. J.; Wiberg, K. B. J. Am. Chem. Soc. 1992, 114, 523 https://doi.org/10.1021/ja00028a019
  20. Boys, S. F.; Bernard, F. Mol. Phys. 1970, 19, 553 https://doi.org/10.1080/00268977000101561
  21. Ventura, O. N.; Coitio, E. L.; Irving, K.; Iglesias, A.; LLeds, A. J. Mol. Struct. (THEOCHEM) 1990, 20, 427
  22. Davidson, E. R.; Chakravorty, S. J. Chem. Phys. Lett. 1994, 224, 166 https://doi.org/10.1016/0009-2614(94)00523-0
  23. Kim, J.; Lee, S.; Cho, S. J.; Mhin, B. J.; Kim, K. S. J. Phys. Chem. 1995, 89, 839 https://doi.org/10.1021/j100251a025
  24. Kim, K. S.; Mhin, B. J.; Choi, H. S.; Lee, K. T. J. Chem. Phys. 1992, 97, 6649 https://doi.org/10.1063/1.463669
  25. Kim, K. S.; Lee, J. Y.; Choi, H. S.; Kim, J.; Jang, J. H. Chem. Phys. Lett. 1997, 265, 497 https://doi.org/10.1016/S0009-2614(96)01473-X
  26. Choi, H. S.; Suh, S. B.; Cho, S. J.; Kim, K. S. Proc. Natl. Acad. Sci. USA 1989, 95, 12094 https://doi.org/10.1073/pnas.95.21.12094
  27. Reed, R. E.; Curtiss, L. A.; Weinhold, F. Chem. Rev. 1988, 88, 899 https://doi.org/10.1021/cr00088a005
  28. Glendening, E. D.; Weinhold, F. J. Comput. Chem. 1988, 19, 610 https://doi.org/10.1002/(SICI)1096-987X(19980430)19:6<610::AID-JCC4>3.0.CO;2-U
  29. Williams, I. H.; Maggiora, G. M.; Schowen, R. L. J. Am. Chem. Soc. 1980, 102, 7831 https://doi.org/10.1021/ja00547a001
  30. Williams, I. H.; Spangler, D.; Femec, D. A.; Maggiora, G. M.; Schowen, R. L. J. Am. Chem. Soc. 1983, 105, 31 https://doi.org/10.1021/ja00339a008
  31. Bentley, T. W.; Carter, G. E.; Harris, H. C. J. Chem. Soc. Perkin Trans. 2 1985, 938
  32. Bentley, T. W.; Jones, R. O.; Koo, I. S. J. Chem. Soc. Perkin Trans. 2 1994, 753
  33. Koo, I. S.; Yang, K.; An, S. K.; Lee, C.-K.; Lee, I. Bull. Korean Chem. Soc. 2000, 21, 1011
  34. Koo, I. S.; Yang, K.; Park, J. K.; Woo, M. Y.; Cho, J. M.; Lee, J. P.; Lee, I. Bull. Korean Chem. Soc. 2005, 26, 1241 https://doi.org/10.5012/bkcs.2005.26.8.1241
  35. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; William Clowes & Sons, Ltd.: London, 1976
  36. Mitchell, D. J.; Schlegel, H. B.; Shaik, S. S.; Wolfe, S. Can. J. Chem. 1985, 63, 1642 https://doi.org/10.1139/v85-276
  37. Shaik, S. S.; Schlegel, H. B.; Wolfe, S. Theoretical Aspects of Physical Organic Chemistry. The $S_N2$ Mechanism; Wiley: New York, 1992

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